Top Tech Jobs & Startup Jobs

Lead the technical strategy and evolution of Headway’s billing platform, including a financial state-machine orchestration layer, guardrail APIs, remittance ingestion, refunds, recoups, reconciliation, and explainability. Manage platform engineering teams, establish technical standards, coordinate cross-functional dependencies, and partner with Finance and Accounting to ensure accurate, auditable financial records at significant scale.

Own the product strategy and delivery of Headway’s payer and patient outcomes data infrastructure. Build patient segmentation, cost-of-care measurement, and payer-facing data products while defining data architecture and priorities. Partner closely with data engineering, data science, clinical strategy, and commercial teams to create auditable, predictive, and externally defensible outcomes and cost insights.

Partner with Engineering leaders to develop and execute people strategies supporting organizational growth. Advise managers on performance management, talent planning, organizational design, leadership development, and employee experience. Use workforce data to identify trends and guide decisions, coach managers, lead HR programs, and collaborate with Total Rewards, People Operations, Legal, and Talent Acquisition teams. The role also promotes cultural integrity, inclusion, accountability, and scalable operational excellence.

Own escalated IT support issues and identify systemic fixes. Manage network health, wireless infrastructure, VLANs, multi-ISP failover, and conference room AV across three offices. Provide after-hours and event-day support, administer identity, collaboration, service management, and endpoint platforms, and deliver office technology projects from design through cutover. Build automation, monitoring, documentation, and runbooks while partnering with Workplace Experience, Security, and Employee Experience.

Own the strategy and roadmap for patient-provider search, retrieval, ranking, and marketplace matching. Lead experimentation, objective functions, evaluation, and ML platform foundations while partnering with ML engineers, data scientists, design, clinical teams, and executives. Improve successful, lasting care matches rather than optimizing only clicks or bookings. Balance patient access, provider growth, clinical quality, and payer priorities, while setting the standard for technically grounded product management.

Lead Headway’s customer experience operation across Agent Success, Customer Care, Programs, and Systems, managing over 100 employees and 800 partner agents. Own end-to-end support quality, performance, staffing, forecasting, costs, training, QA, procedures, systems, and AI-enabled automation. Partner with Product and R&D to improve customer experience and reduce support demand while developing a high-performing leadership team.

Owns the full business development cycle for mid-market health system partnerships, including prospecting, qualification, pitching, closing, and launch. Builds relationships with care management, population health, and clinical operations leaders; develops account strategies; supports enterprise opportunities; and collaborates with Partner Success, Product, and Operations to ensure successful referrals and launches. Also mentors the BDR team.

Owns commercial KPI production, competitive intelligence resources, reporting cycles, and enablement infrastructure for Headway’s payer partnerships organization. The role drives strategic and operational workstreams, coordinates commercial reporting, supports team scaling, and applies AI tools critically to produce reliable recommendations. Success requires strong operational execution, resourcefulness, analytical problem-solving, and comfort working in ambiguity within a digital health environment.

Lead and grow a data science team focused on provider experience. Define strategy, build roadmaps, run analyses, experiments, and predictive models, surface insights, and partner cross-functionally to drive measurable improvements in provider engagement and product experience.

Own the operating rhythm and planning system for Headway’s R&D organization. Responsibilities include quarterly and annual planning, headcount and capacity prioritization, leadership meetings, board preparation, decision memos, escalation processes, organizational design, budget governance, and cross-functional alignment across Product, Engineering, Data, and Design. This Director-level individual contributor role solves high-priority, ambiguous organizational problems and drives execution through influence rather than authority.